Methyl 2-(6-(benzyloxy)-5-phenylpyridin-3-ylamino)-5-cyclopropylbenzoate → HCID 178524103, compound

HRID 42056Notes

Reaction equation

HRID 42056 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:28][CH2:27]3)=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:11][C:10]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH:26]1([C:23]2[CH:24]=[CH:25][C:16]([NH:15][C:12]3[CH:13]=[N:14][C:9]([OH:8])=[C:10]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:11]=3)=[C:17]([CH:22]=2)[C:18]([OH:20])=[O:19])[CH2:27][CH2:28]1

Participants

3

Reactant 1

HCID 67394538Methyl 2-(6-(benzyloxy)-5-phenylpyridin-3-ylamino)-5-cyclopropylbenzoate

Product 1

HCID 178524103HCID 178524103, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 2-(6-(benzyloxy)-5-phenylpyridin-3-ylamino)-5-cyclopropylbenzoate (0.34 mmol, 0.155 g) in TFA (1.3 ml) was stirred at 45° C. for 30 minutes. The solvent was removed under reduced pressure. The crude mixture was solved in ethanol (2 ml), 2N aqueous NaOH were added and stirred at room temperature for 16 hours. The solvent was removed and the crude was neutralised with 2N aqueous HCl and extracted with CHCl3. The crude mixture was purified by ionic exchange through a SCX cartridge affording 0.060 g (50% of yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. addition2N aqueous NaOH were added
  3. customThe solvent was removed
  4. extractionextracted with CHCl3
  5. customThe crude mixture was purified by ionic exchange through a SCX cartridge
  6. customaffording
  7. custom0.060 g (50% of yield)

Sources & evidence

ORD record
ord-c915df7c41ed40f79bf84532c54bfa1a
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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